The whole ensemble really looks so classic, yes equestrian, and fits you well. The red highlights your lovely complexion and hair. The whole thing works as does the marled jacket outfit. Fun to see the outfits as they speak of today despite their past purchase. You definitely have pieces that are workable but fall in line with current style.

I struggle posting this comment, because usually I post only when I have something amusing or complimentary to say, but in the interests of a diverse comment section… I’m afraid that jacket really, really looks like it’s from the early 2000’s to me. Like something Suze Orman would have worn in early days (except in leather).

Keep the skirt and boots! (though I do think I’d like the boots better with black tights) but perhaps swap in a longer structured sweater (a low V?) rather than the boxy knit?

And thus began The Directrice Flame Wars! But your comment is respectful and I can see what you are saying (oh no!), so I doubt it will touch any nerves. I appreciate all of your comments, Cat! I tell The Photographer before publishing half of my posts, “They can’t all be the best post.” (I do, however, somehow think that the other 50 % are the best post.) This does make me wonder what Suze Orman plans to be buried in . . .

In case it helps, I’ve been getting good mileage out of my somewhat-cropped tops (that is, ending at or above the hip, like the jacket in question), even the ones from the early-2000s, atop the high-waisted ankle-baring culottes which seem to be having a fashion moment this year.

(not that I advocate any ankle-baring until the weather warms back up)

Tricky, but there are very few true clothing “classics” to me (accessories do fare better). I try not to purchase one-season type trendy items (see: off-the-shoulder or cold-shoulder anything) but even trying to stick to the most timeless of purchases, proportions shift gradually… like the proverbial frog in warming water, it can be hard to tell the line when a former “classic” transitions to “oh that jacket is so 80’s!”

Lapels and collars widen and shrink (I recently tried on one of my go-to blouses from the early 00’s and was struck by how much longer/pointier the collar is compared to more recent purchases), proportions and lengths vary (for example, pants with a wide waistband and narrow belt loops strike me as early 00’s also; ankle pants are great now, but just a few inches shorter and you’re rocking 1998 capri pants).